


Pretty Boy

by Im_A_Terrible_Person, sourbby



Series: Requests :) [15]
Category: Real Person Fiction
Genre: Angst, Angst and Fluff and Smut, Anxiety, Bottom Wilbur Soot, Emotional Hurt/Comfort, Established Relationship, Feels, Fluff, Fluff and Smut, Hurt/Comfort, Insecurity, Light Angst, M/M, Mutual Masturbation, Panic Attacks, Phone Sex, Smut, Top Jschlatt (Video Blogging RPF), discord sex, pillow humping, sorta - Freeform
Language: English
Status: Completed
Published: 2021-03-12
Updated: 2021-03-12
Packaged: 2021-03-19 03:47:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,282
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29993391
Author URL: https://archiveofourown.org/users/Im_A_Terrible_Person/pseuds/Im_A_Terrible_Person, https://archiveofourown.org/users/sourbby/pseuds/sourbby
Summary: Schlatt's gift arrived at the most inopportune time.
Relationships: Jschlatt/Wilbur Soot
Series: Requests :) [15]
Series URL: https://archiveofourown.org/series/2193852
Comments: 4
Kudos: 222





	Pretty Boy

**Author's Note:**

> For @Z03222 <3
> 
> Sorry, I couldn't find the energy to write a fluff outtake tonight. Might add one tomorrow.
> 
> Tell me if there's anything you want me to change :D

It was the first time they’d streamed together since they had got together. Wilbur was nervous, paranoid that his viewers could tell, could tell by the love-struck grin on his face as he listened to Schlatt. He was doing a bit, probably a funny one, but he wasn’t paying attention to his words, more to his cadence, his accent, the little throaty flair.

“Wilbur? Wil, you all right?” Schlatt’s voice had a sarcastic edge, something mean to take away from his concern. Wilbur saw through it. 

“Yeah. Sorry, I spaced out.” Wilbur coughed, ran a hand through his hair. He tried to focus more on Schlatt as the night went on, but he’s not sure he succeeded. His chat noticed something distracted him, but just assumed he was tired. A few suggested it was Schlatt, but defenders came to his defence, told them to stop sexualising every little interaction between him and his friend.

Kind of them, but it made Wilbur’s gut twist with guilt. They were right, weren’t they? Though it was probably a fluke, they said the same thing about Dream and George, Dream and Sapnap, Schlatt and Quackity. He knew they weren’t right about those; it was a coincidence that they were right about this. That calmed his nerves, just a bit, but his heart still pounded. Fuck.

“Wilbur? Wil? Wilbur? Dude, your doorbells going off, you need to get that.” God, he was being so obvious. Wilbur stood up, fixed his clothes, and left. He tried to calm himself down. What, was he _trying_ to get exposed? No, but he was acting like it. 

He sighed, stepped out into the hall, closed the door behind him. Okay. They couldn’t see him. Couldn’t hear him. He was fine. Time to get the package. Wilbur felt a bit stupid for assigning such importance to such a mundane thing, but he needed something to ground him. Just grab the package, that’s all he needed to do.

Wilbur wasn’t expecting a package, he realised. He didn’t know what it could contain. Had he ordered something late at night, forgotten? Wilbur didn’t think so; it would have charged to his card, would have noticed it somehow. Had Schlatt sent him something, not told him?

Perhaps. Now Wil was curious; what could it be? If Schlatt sent him something, it was bound to be a bit tongue in cheek, maybe perverted in some way to get the chat to go crazy. He hoped not, he couldn’t handle that right now. Wouldn’t be able to cope if he had to try to make lewd jokes on stream without devolving into… actual lewdness.

He opened the door. Fairly unassuming, a normal Amazon package. Wilbur picked it up, closed the door behind him. Did he open it out here or with chat? With chat, they’d badger him about it if he didn’t. Wilbur went back into the room, holding the package. It wasn’t heavy, pretty light. A poster, something like that, paper? He sat back down, placed the box in his lap with a teasing grin, ready to go. 

“Am I going to get banned if I open this, Schlatt?” Okay, good, he sounded normal.

“Nah, should be fine.” So it was from him. Interesting.

Well. Might as well. Wilbur grabbed some scissors, opened it. Schlatt started interacting with chat, keeping them occupied as he tore the box open. Little plastic bags of air, a nice pale green. He pulled them out, let them fall to the floor as he took in what Schlatt had paid an international shipping fee to send him.

“Schlatt.” No. He’d already opened it, there was no way he could get away without showing chat. This wasn’t funny. 

“Yeah?” Schlatt sounded so smug. Wilbur wasn’t in the mood.

“What the fuck is this?” Fuck, he didn’t mean to sound that angry. He could almost hear the humour drain out of Schlatt. But they couldn’t give up now, there were too many people watching. Schlatt was quick to come to the rescue.

“I don’t know. Why don’t you show me?” The right tone, just flirty enough. God, he hated this. This joke was months old, not even funny to them anymore. Schlatt had sent him this because he wanted Wilbur to wear it for him and he’d fucked it up by opening it on stream. At least it would come off as a gimmick, a little fan service type thing.

“Alright, one minute.” He got up again, took the package away. He caught a glimpse of chat, mostly full of people begging him to show them what was in the box. Fuck that. Fuck this. Wilbur wanted to end stream right now, to just leave and rip into Schlatt for embarrassing him like this. 

Wilbur shut himself in the bathroom, took a few deep breaths. Okay, he was doing this. This was a thing that he was doing. He could do this. This was fine. He sighed out, running his hand through his hair to calm himself down, then upended the package over his sink. All frills and lace. Wilbur’s face reddened as he took in just how much there was. This couldn’t have been cheap, could it? Why had Schlatt spent so much just to send Wilbur a… a… a _maid dress?_

Wilbur couldn’t take too long with this, even if he wanted to hide in here forever. He stripped as quickly as possible, dropping his clothes all over the floor in his haste. Wilbur didn’t care; he wanted to get this over as soon as possible. The faster the better. He didn’t put a whole lot of care into putting the outfit on. It was a dress, not that hard to figure out how to slip it over his head, how to get it to sit right on his… not exactly feminine body. 

He looked himself over in the mirror, cringing at how it clung to him, showed off his lack of muscle, the way his collarbones jutted out so much, so obvious. Wilbur hated it. Hated this. Hated every second. But he’d have to own it, have to go out there and act like he thought of himself as the hottest thing ever, tease Schlatt like this looked good.

Wilbur almost wanted to text his roommate, ask him to come up with an excuse and end his stream for him. But that’d be suspicious, so he just had to… go through with it. He spent about thirty seconds just psyching himself up before heading back in, grin plastered on his face. He’d come up with a bit, everything’d be fine.

That plan was impossible the second he stepped out into the air of his apartment, suddenly all too aware of the silence, of the fact that he was a grown man in his twenties about to prance around in a maid outfit on camera for people to clip, spam him with those clips, laugh at him for thinking this was in any way a good idea.

No, he’d sit down and act like nothing had changed. Easier than trying to think up a good joke while he was panicking, that’s for sure. Yeah, that sounded nice. Just sit down, go back to talking to Schlatt like he wasn’t wearing a fucking maid costume. All short and frilly, so pretty. If only he wasn’t the one wearing it, it’d look beautiful. 

Wilbur forced himself to go back into the room, despite everything screaming at him that he should just hide, run, fucking _run_. He didn’t look at chat as he sat down, clicking through some random stuff on his computer so it seemed like he was doing something. 

Fuck, it was hard to breathe. He looked so fucking stupid, didn’t he, and chat was probably spamming ‘ew’ and ‘cringe’, his viewership was going down, he was so fucking ugly, so fucking dumb, Wilbur should’ve just ended stream, never opened up Twitch again, deleted all his social media.

-

Jesus fucking Christ, Wilbur was _gorgeous._ Schlatt had to pause for a second, just to take him in. Only a second, any longer than that and he would have seemed suspicious. Wilbur wasn’t looking at the camera, wasn’t looking at chat, wasn’t looking at Discord. He recognized the faux calm, the way Wilbur kept his eyes trained on the screen like this was Bird Box, like the monsters were everywhere except that one monitor.

Wilbur looked so pretty, the dark lace emphasizing his curves, how long his legs were, how thin he was. Schlatt knew he hated it, hated how he could see his ribs, his collarbones, the ridges of his spine. Schlatt thought he was beautiful, loved how small he felt beneath his baggy hoodies.

Unfortunately, he couldn’t say that here. There were fifty thousand people watching this, the number only climbing higher as more people clicked onto the stream, hearing that the Wilbur Soot had dressed up in a maid dress sent to him by Jschlatt. God, why did it have to arrive now? He’d been looking forward to Wilbur putting on a show, complimenting him, watching him blush, watching him slip a hand under his skirt, maybe grind against a pillow, moaning Schlatt’s name.

“You look good.” Instead, he had to half-joke with Wilbur, toe the line between flirting and joking for the entertainment of thousands. God, why had he chosen to do this? 

“I know.” A fake, cocky grin as Wilbur looked into the camera. That smile sickened Schlatt, made his heart drop. That smile means Wilbur was panicking, plummeting, world closing in around him as people looked on, hungry for more. Schlatt hated that smile, knew it meant Wilbur was hating himself, hating his body.

“Give me a twirl?” This wasn’t supposed to go like this. He was supposed to praise Wilbur, to make him blush, to watch him get all needy and soft for him, let himself get honest with Schlatt. 

“No, I don’t want to get up again.” A lie, even chat could tell it. They probably thought it was because he might get banned. The skirt was awfully short, Schlatt had gotten it because he wanted to see Wilbur in something pretty, but something that still exposed him. Something that Wil would be comfortable in, something that covered him enough to keep him from getting too insecure. 

Wilbur started answering questions, ignoring one’s asking him what he was wearing. Schlatt tried to praise him, compliment him as much as possible. It wasn’t enough. He always had to have that joking tone, lay the sarcasm on so thickly he almost convinced himself. He hated the despair in Wilbur’s eyes as he watched the clock, tried to keep up appearances long enough for it to be unsuspicious when he ended stream.

Schlatt felt the time crawl by, so slow, so awkward. He wanted to talk to Wilbur, make him feel better, but he couldn’t. Had to watch, helpless, as Wilbur said goodbye to his viewers, ended the stream as fast as possible without it being odd. Schlatt said goodbye too, couldn’t bring himself to make a joke. He was far too worried to think up a bit, making sure Wilbur had really stopped streaming before leaning forward, turning his camera on.

“Wil? Wil, look at me.” Schlatt’s voice was soft. Now wasn’t the time to be loud, to be ordering Wilbur around. Wilbur did, but he’d hunched in on himself, slouched down in his chair as far as he could, trying to disappear from the viewfinder. Schlatt’s heart hurt, looking at him. His eyes looked so scared, blurry with unshed tears.

“What’s wrong?” Wilbur made an angry noise, glared at the monitor like he wanted to strangle Schlatt. Right, dumb question.

“I’m sorry. I didn’t want this to happen on stream.” He kept his voice quiet, sincere. 

“Why? What were you hoping for?” Wilbur’s voice was bitter, upset.

“I wanted to see you in it.” He did, still did. Fuck, he wanted to see Wil. Schlatt wished that he was there, there so he could hug Wilbur, kiss him until he couldn’t remember what he’d been insecure about in the first place. Instead, he was stuck watching Wilbur through a screen, loving him from afar. 

“So? You happy? This what you wanted?” Wilbur scoffed, stood up. Tugged angrily on the skirt, the sight made Schlatt’s mouth go dry. Wilbur was slender, delicate, the skirt only emphasized how petite he was. 

“Yeah. You’re hot.” Not the time for levity. Wilbur didn’t take it well, left the sight of the camera. Wait, was he going to change?

“Wilbur. Wil, come back. I want to see you.” Dead serious. Wilbur complied, placed his hands on the arm of the chair and stared at the screen, waited for Schlatt’s next instruction. He looked so nervous, so scared. Schlatt didn’t like that, hated the panic in Wilbur’s eyes as he looked on.

“You’re beautiful.” Such a cheesy line, but it was true. Wil looked so pretty, all dolled up for him in his cute little dress. Even as he scowled at Schlatt, disbelieving.

“I’m serious. You’re so fucking pretty, Wilbur. Absolutely gorgeous. Cute.” Schlatt moved closer to his mic, dropped his voice half an octave. He saw Wilbur shiver, close his eyes. Yes, more of that. 

“Really?” Wil’s voice was small. A plead for more.

“Yes, really. So pretty. So good for me. Right, Wilbur? You’re my good boy?” Schlatt murmured. Wilbur flushed, red all the way down to his collarbones. God, he was so fucking cute.

“Yeah.” Wilbur choked. He still looked scared, but there was an eagerness there, a want to please Schlatt. 

“Say it.” A simple order, something light to start them off. Wilbur squirmed a little, sat down in his chair again and looked into the chapter.

“I-I’m your good boy?” Schlatt shivered. Fuck.

“Again.” 

“I’m your good boy.” His voice was a bit stronger this time, more sure of himself. Pride swelled in Schlatt’s chest. He was making Wil feel better, Wilbur was being so good for him, following his orders.

“Good boy. Think you could move your camera a bit? Show your bed?” A bit more taxing this time. Wilbur complied, adjusted the camera so it had a view of his bed. Schlatt hummed his approval.

“Get on it.” Schlatt moved a hand to rest on his thigh as he watched Wilbur climb onto the bed, fabric brushing against his thighs as he crawled to the center before settling so he was facing Schlatt. God, how could he make such simple movements look so sinful? Everything felt seductive, dark, lewd as Wilbur sat on the bed, legs folded beneath him. Wilbur hadn’t even done anything sexual yet, had just followed some of Schlatt’s orders, had gotten into bed, but he was just so fucking hot.

“Wil, could you grab a pillow for me?” He popped the button to his jeans, unzipped them as Wilbur did, hugged the pillow to his chest. The maid dress was simple in its design, a black skirt and white apron with a few white lace details and frills. It had cost him a lot, he’d had to really convince himself that it was worth it before buying, but it looked so fucking good on Wilbur.

"Ride it.” Wilbur hesitated, just for a second, before complying. He rose up on his knees, spread his legs so he could slip the pillow between them. Wilbur sat down, breathed out shakily. Schlatt didn’t push him to move, not yet. This was more than enough for him. Wilbur rested his hands on the sheets in front of him, leaned forward. 

“Good boy, Wil.” His voice was rough, he pushed his jeans down just enough so he could get his dick out, not getting himself off yet. No, he’d wait a bit for that.

“Move.” One word. Wilbur sucked in a breath, held it as he rocked against the pillow, rolled his hips down into it. The dress swished around Wil’s legs as he gasped, did it again. Built up a rhythm, mewling quietly as he rocked his hips.

“Schlatt.” Wilbur moaned breathily, moved his hips faster. Schlatt started stroking himself, throat clicking as he swallowed. Jesus fucking Christ. Wilbur’s hair fell into his eyes as he looked at Schlatt, giving him this almost ethereal look. Schlatt groaned, low in his throat as he watched Wilbur rut against the pillow, watched him moan Schlatt’s name.

There was nothing sexually explicit about it, not really. The skirt hid Wilbur’s cock, only tenting up when he rocked forward just right, hips stuttering as he whined. But something about not being able to see but still knowing he was getting off, watch him squeeze the pillow between his thighs, watched him thrust faster, whimpering so prettily.

“So pretty. You look so good right now, you know? I wish I was there, wish I could fuck you like that. Would you ride my cock like that, Wil? Sit on my lap, bounce for me? Be good for me?” Schlatt groaned, speeding up the hand on his cock as he leaned forward, drinking in the image of Wilbur losing himself in this, dropping his head down against his chest as he cried out. 

“Y-yeah. I would. Schlatt, fuck.” He babbled, fingers twisting in his sheets as he put more weight on his hands, thighs trembling.

“Hang on for me, Wil. You can do that, right? Be good for me, baby.” Wilbur sobbed as he forced himself to slow down, hips jerking against the pillow. He kept his pace slow, whining at the loss of friction. Fuck, just for Schlatt. He denied himself just for Schlatt.

“Schlatt, please.” Tears spilled over Wilbur’s cheeks as he begged, looked into the camera. He looked so desperate, so needy, so owned. Owned by Schlatt. All his, he was the only one who got to see Wilbur like this. Schlatt tightened his grip, moaned loudly as he arched his hips up into it. 

“Just a bit longer.” God, Wilbur looked so pretty when he cried. His face was already so red, but the tears made his eyes dewy, wet. His cheeks were shiny, mouth open as he cried, pleaded with Schlatt to just let him cum.

“Go ahead. Cum for me, Wilbur. Fuck, such a good boy, such a good boy for _me_ , all mine. You’re my pretty boy, aren’t you Wil? My pretty little Wilbur, all dressed up for me, being so good for me. Cum for me, yeah? Be good for me?” He groaned, soft and low as he jacked off, eyes focused on Wilbur as he sped up again, skirt bouncing as he whined, hips stuttering.

“Schlatt, _Schlatt_ , fuck, Schlatt, please, God, I-I-” He mewled, hips jerking as he came all over his pillow. The sight pushed Schlatt over the edge, cumming all over his fist and his jeans with a groan.

“Wilbur? You good?” Schlatt wiped his hand off on his jeans, taking them off the rest of the way. He could deal with that later.

“Yeah. Fuck, Schlatt.” Wilbur laughed, breathless. He got off the pillow, approaching his computer again.

“Yeah?”

“I’m going to be seeing clips of that for the rest of my life, aren’t I?”

“I thought you stopped the stream? Don’t tell me you just humped a pillow in front of you fans, dude, that’s just weird.”

“Schlatt. That’s not what I meant.”

“I know. You’re just so cute when you blush.”

“Shut up, Schlatt. I need to go put these in the wash. Be right back.”

“Love you.”

“Love you too, but I don’t want to ruin this dress.”

“You gonna wear it again for me?”

“Shut up.”

**Author's Note:**

> One fic away :)


End file.
